My Octopus Teacher: Jake Shane

Thu May 29 2025

What's that delicious smell in the shady Manhattan studio today? Well Grace is joined by comedian, internet superstar, and therapuss-in-residence Jake Shane to find out! The two catch up on the near-arrest that defined their last hang, Jake’s viral rise and Hacks cameo, and the fajita fiasco heard around the world. They dive into tour life, podcasting anxiety, Jake's Lisa Barlow impression, and the shift from Brat Summer to Lorde Summer. Jake opens up about his slept-on music era and faces off with Grace in a game of “Who’s More Disgraceful” that involves Ed Sheeran, public shame, and friendship trauma. It's all in a day's work, kids. Have a day, much love, & enjoy the show!

Transcript

Grace O'Malley (0:00)

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Summary

Podcast Summary: "Disgraceful with Grace O'Malley"
Episode: My Octopus Teacher: Jake Shane
Release Date: May 29, 2025

Introduction

In the episode titled "My Octopus Teacher: Jake Shane", host Grace O’Malley welcomes comedian and actor Jake Shane as her special guest. This episode centers around Jake's journey in the entertainment industry, his experiences touring, and his collaboration with Grace on various projects. The conversation is laced with humor, personal anecdotes, and insightful discussions about the challenges and triumphs of being in the public eye.

Guest Introduction and Personal Stories ([11:02] - [17:38])

Grace enthusiastically introduces Jake Shane, highlighting their longstanding friendship and previous collaborations. Jake shares memorable moments from their past, including sending him a heartfelt thank-you video and their first podcast experience together.

Grace O’Malley [11:13]: "I am super jazzed, super excited, super stoked to have my friend hilarious, amazing, can do no wrong, Jake Shane in the building today."

Jake Shane [15:41]: "I think that's the way to do it."

Jake recounts his initial fears of stepping into the acting world, particularly his audition for the acclaimed show Hacks. He describes the supportive environment on set, contrasting it with the often tense dynamics portrayed on screen.

Jake Shane [16:15]: "It was one of those experiences where you're like, oh, I see why this show is as successful as it is because the environment is so good when creating it."

Touring Experiences and Coping Mechanisms ([17:39] - [26:07])

The discussion shifts to Jake's experiences while touring. He details the rigorous schedule, the balance between performing and exploring new cities, and the challenges of maintaining personal well-being on the road.

Jake Shane [25:09]: "But then I think it's got, like, a little too serious for a second."

Grace shares her own strategies for staying grounded during tours, emphasizing the importance of having supportive companions.

Grace O’Malley [25:50]: "So when you're touring, how do you... I try to see a little bit of the city when I'm there, but it's hard."

Podcast Co-Host Audition Segment ([30:22] - [45:55])

Grace introduces a playful segment where she auditions Jake as a potential co-host for her podcast. Through a series of humorous and thought-provoking questions, they assess each other's suitability for the role.

Grace O’Malley [30:24]: "So I have each guest come on and I ask them a series of questions to see if they'd be a good fit."

Jake Shane [31:18]: "Honestly, you can't just go around calling people crazy."

They engage in light-hearted banter, sharing personal stories and discussing their growth as podcasters. This segment showcases their chemistry and mutual respect, highlighting why Jake is a strong contender for the co-host position.

Interactive Games and Audience Engagement ([45:55] - [58:43])

The duo transitions into interactive segments, including rapid-fire pop culture questions and storytelling games. These segments not only entertain but also reveal deeper aspects of their personalities and friendships.

Grace O’Malley [70:07]: "What's the strangest TikTok algorithm you've been stuck in?"

Jake Shane [73:22]: "Always, always, always the Society."

Their playful interactions create a lively and engaging atmosphere, making listeners feel like part of the conversation.

Reflections and Future Endeavors ([58:43] - [100:04])

Grace and Jake reflect on their past experiences, discuss their favorite moments, and share plans for future projects. Jake opens up about his songwriting process, highlighting his collaboration with producer Alexander and his passion for creating meaningful music.

Jake Shane [63:17]: "It's called 'Santa, can you pay for me in parentheses. I forgot my card.' That's classic."

Grace offers valuable insights into overcoming self-doubt and building confidence, drawing from her own podcasting journey.

Grace O’Malley [50:01]: "I'm so glad you said that, because there really is only one answer. She was the best to ever do."

Conclusion

The episode concludes with a heartfelt exchange of shout-outs and well-wishes between Grace and Jake. They reminisce about shared memories, express gratitude for each other's support, and solidify their bond as friends and collaborators.

Jake Shane [99:54]: "If you want to see my live show, you can get tickets@passthatpuss.com and stream therapists, which is out every Wednesday at 7pm Pacific."

Grace O’Malley [100:04]: "Thank you so much for coming. This has been amazing. I love you so much. You rock."

Notable Quotes with Timestamps

Grace O’Malley [11:13]: "I am super jazzed, super excited, super stoked to have my friend hilarious, amazing, can do no wrong, Jake Shane in the building today."
Jake Shane [16:15]: "It was one of those experiences where you're like, oh, I see why this show is as successful as it is because the environment is so good when creating it."
Jake Shane [63:17]: "It's called 'Santa, can you pay for me in parentheses. I forgot my card.' That's classic."
Grace O’Malley [50:01]: "I'm so glad you said that, because there really is only one answer. She was the best to ever do."

Key Takeaways

Authentic Connections: The episode underscores the importance of genuine relationships in the entertainment industry, as exemplified by Grace and Jake's friendship.
Overcoming Anxiety: Both hosts share strategies for managing anxiety and maintaining mental well-being amidst the pressures of fame and touring.
Collaborative Creativity: Jake's insights into his songwriting process highlight the value of collaboration and creative partnerships.
Engaging Audience: Through interactive segments and relatable anecdotes, Grace and Jake demonstrate effective ways to engage and entertain listeners.

This episode of "Disgraceful with Grace O’Malley" offers a blend of humor, heartfelt moments, and insightful discussions, making it a compelling listen for fans and newcomers alike.